HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ethyl 3-cyclopropyl-3-(6-(hydroxymethyl)pyrimidin-4-yl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylpropanoate | HCID 131736020 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl 3-cyclopropyl-3-(6-(hydroxymethyl)pyrimidin-4-yl)propanoate | HCID 117759635 | 71.1% |
Reaction Steps
To a solution of ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylpropanoate (6.70 g) in THF (50 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in THF (27.4 mL) at room temperature, and the mixture was directly stirred for 5 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.44 g) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382188B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-3cfb3e04dfb2402fbe5829835701e665 |
| Source note | uspto-grants-2016_07 |